Chicago Sightseeing Tours & Cruises tours

Chicago Sightseeing Tours & Cruises - Page 5

329 experiences to discover

Air & Helicopter Tours City & Sightseeing Tours Cruises & Sailing Tours Cultural & Theme Tours Day Trips & Excursions Multi-Day & Extended Tours Private & Custom Tours Shopping & Fashion Tours Walking & Biking Tours

Explore the best sightseeing tours & cruises tours and activities in Chicago. Our unbiased ratings help you find the perfect experiences for your trip.

Sort by:

4.57

Chicago History and Evolution Walking Tour

From $118

1 provider live

Uncover Chicago's vibrant history

Professional and experienced tour guide

4.57

Chicago Sedan Sightseeing Tour 4 hr

From $250

1 provider live

Experience luxury in a private sedan

Private transportation

4.57

Chicago Pedicab Tour with Music 1 hr

From $80

1 provider live

Enjoy a relaxing ride with your favorite music

Private pedicab tour of Chicago

4.57

Chicago Private Tour

From $300

1 provider live

Explore iconic Chicago landmarks

Guide languages in English and Spanish

4.57

Chicago Blues Concert Aboard Tall Ship

From $81

1 provider live

Sail on the iconic Tall Ship Windy

Access to all ship amenities (restrooms, bar, seating areas)

4.57

Chicago Architecture, Art and History Tour

From $95

1 provider live

Explore iconic Chicago buildings

Amazing experience for architecture lovers

4.57

Chicago City Tour Sedan 4 hr

From $640

1 provider live

Explore Chicago in style

50 miles in downtown

4.57

Chicago Tall Ship Sail on Lake Michigan

From $115

1 provider live

Sail on a majestic tall ship

Government Fees

4.57

Chicago Walking Tour of Pullman Historic District

From $223

1 provider live

Explore a National Monument

Bottled water

4.57

Chicago to Milwaukee Biking Tour

From $349

1 provider live

Explore the scenic route from Chicago to Milwaukee

Route planning and safety vehicle

4.57

Chicago River Brunch Cruise

From $164

1 provider live

Savor a delicious plated brunch

Delicious plated brunch with freshly prepared entrees, salads, and desserts

4.57

Chicago Family Odyssey Tour

From $665

1 provider live

Embark on a private family adventure

Professional local guide services